I’m sure you can do it, but I haven’t seen anything, so here goes: Can you deploy non-web (test harnesses, exe’s, etc.) apps as well as IIS and Rest stuff?
Thanks for getting in touch! The rule of thumb is if you can package your files in a NuGet package, and install Tentacle in the target machine, Octopus can deploy it.
You might need to write custom PowerShell scripts, but it can be done.
An example of MSI installation with Octopus: http://octopusdeploy.com/blog/install-msi-with-octopus
Hope that helps!